Joshua Boyle, now free after five years of captivity in Afghanistan, is perhaps best known for his brief marriage to Omar Khadr’s older sister.

Boyle, the son of an Ottawa tax court judge, was married for about a year to Zaynab Khadr. She’s the eldest daughter of Ahmed Said Khadr, who was accused by the U.S. and Canada of being an associate and financier for the terrorist group Al-Qaeda. Ahmed Khadr studied at the University of Ottawa, and the family moved between Canada, Afghanistan and Pakistan.

Zaynab Khadr was a fierce defender of both her father and her brother, Omar Khadr, who was captured as a 15-year-old fighting with the Taliban in Afghanistan and charged with killing an American soldier.

How did Zaynab Khadr meet Boyle, a University of Waterloo graduate? Boyle had developed a keen interest in national security and human rights issues after the terrorist attacks of 9/11.

Boyle was principled, smart and a “crusader” by nature, said his friend Alex Edwards, who lives in Carleton Place. Boyle was captivated by the plight of Omar Khadr, who was being held in a U.S. prison in Guantanamo Bay, said Edwards.

“Here was this kid, this Canadian child, off in an illegal American prison, and everyone in (Canada) was vilifying the Khadr family, and Josh decided, ‘Hey, this isn’t right.’ So he went off and devoted several years of his life to help this innocent kid.”

Boyle had no connection to the Khadr family, but introduced himself and volunteered to help them, said Edwards.

Boyle acted as the Khadr family spokesperson in 2008 when Zaynab staged a hunger strike on Parliament Hill to protest her brother’s detention. (After a decade at Guantanamo, Omar Khadr was returned to Canada, and later received a $10.5 million settlement from the Canadian government for violation of his charter rights.)

Boyle married Zaynab Khadr in 2009. He was 25, she was 29. It was the third marriage for Zaynab. The first two were arranged: her first husband was sought as a conspirator in a bombing of the Egyptian Embassy in Pakistan; Osama Bin Laden was one of the guests at her second wedding in Afghanistan.

Back in Canada, Zaynab created controversy in 2004 for controversial remarks she made criticizing the way children were raised here and suggesting that the Sept. 11 terror attacks were justified.

Boyle defended his wife for her earlier remarks. In an email exchange with a Postmedia reporter, Boyle said his relationship with Zaynab had taught him that no one can accurately judge the character of a person they’ve never met.

“Are any of us honestly able to say that we have never uttered any phrases which, if they ran beside our name in the paper every month for five years, would paint an unflattering mental image in the public perception?” he asked, adding, “Let he without sin cast the first stone.”

Edwards said, as far as he knows, Boyle was not devoted to any particular political philosophy. He was a pacifist, anti-war and anti-abortion. “He once described himself to me as a hippie, Mennonite love child.”

Edwards knew Boyle over the course of more than a decade, mainly through an online role-playing Star Wars game. Boyle was a “very private person,” but had a reputation in the gaming world as being both cunning in getting people to do what he wanted and generous to new players, he said.

A few months after Boyle married Khadr, intruders broke into the west-end Ottawa home of his parents, Linda and Patrick Boyle. Patrick Boyle was a federal tax court judge.

Intruders smashed the front door, ransacked the house and left bullet holes in the windows. Nothing of value was taken, Postmedia reported. The Boyles were away at the time.

Joshua Boyle believed the break-in was somehow connected to his marriage.

“I’m sure I don’t have to speculate for you on the meaning of .22 calibre bullets fired from close range through residential windows following an unwarranted break-in by an intruder who left behind all the jewelry, cash and valuables in the house,” he wrote to Postmedia at the time.

“Perhaps somebody is unhappy that the Boyles are highlighting to the public just how human the Khadrs really are,” he wrote. At the time, he was living in Toronto with Zaynab and her daughter from a previous marriage.

The marriage didn’t last long, though. They divorced in 2010.

The next year, Boyle married Caitlan Coleman, a U.S. citizen who grew up in rural Stewartstown, Pa., according to an article in The Inquirer.

The pair met on Star Wars fan sites.

Coleman was home-schooled, according to the Inquirer, which quoted friends describing her as “a woman shaped by rural values, with a big-hearted curiosity about the wider world.”

The couple married while on a hike through Central America, the article said.

In the summer of 2012, they thought they had the experience to handle a backpacking trip to Central Asia, according to a video interview with Coleman’s parents.

Caitlan was pregnant at the time.

Afghanistan was not on their itinerary, so it’s unclear how they ended up there, said the Inquirer.

Boyle and Coleman were used to travelling in places most people don’t go, said Edwards.

The couple had done “freelance aid work” in South America before, so perhaps they meant to do the same in Afghanistan, he speculated.

“We can’t know for sure, but they probably meant to do much the same in Afghanistan and a number of other Central Asian nations,” Edwards wrote in a blog post. “What’s even less clear is why they thought this was a good idea. Joshua has a loose connection to Afghanistan, a deep respect for Islam — he may even have been in the process of converting — and a purely academic interest in terrorism, but none of that even remotely qualifies him to travel safely in Afghanistan. It could have been simple naiveté, but I, and many others, have always known Joshua as an exceptionally cunning and savvy man. Maybe he was overconfident. Maybe he was immature. Maybe this time Joshua just bit off more than he could chew.”

The couple was believed to be travelling in Wardak province in Afghanistan when they were abducted by a Taliban-affiliated group in the fall of 2012.